He abandoned trying to scale.Learning from this experience when my partner and I decided we wanted to double our net income, we realized it would take a increase of 2 1/2 time our volume and probably need to triple our deal flow.  

A coach makes sense if you are 23 and want to increase your skills enough to earn a living with the sport.

A prior cost segregation study increases the depreciation taken during the owner’s lifetime, lowering taxable income each year.

However, San Diego is an extreme case.However rents increase fast in San Diego.  

There are a lot of ways to crash and burn, so increasing the odds of succeeding long term should be your highest priority. you can always sell your local assets once you're comfortable managing rentals and ready for a market that better-suits your criteria. btw, kudos for being self-aware of your limitations.

With VRBO, strangely, it keeps recommending significant increases which isn't wrong.

It has gotten increasingly frustrating to deal with inadequacies and complaints from my tenants as far as payment processing.

Ditch the red rug, increase art and add dresser, bedside tables to bedrooms.

You can find SF properties that already have in law suites, garage units, etc, and now legally rent those, so it should increase the appraised value significantly.

You are already paying rent, so pay it to yourself to increase cash flow and accelerate savings for the next investment.